3,4-dihydro-2H-pyran → 6-(Bromomethyl)-1-(tetrahydro-2H-pyran-2-YL)-1H-indazole

HRID 1634151Notes

Reaction equation

HRID 1634151 reaction equation
Br.[Br:2][CH2:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[N:9][NH:10]2)=[CH:6][CH:5]=1.[O:13]1[CH:18]=[CH:17][CH2:16][CH2:15][CH2:14]1>C1COCC1.C(Cl)Cl>[Br:2][CH2:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[N:9][N:10]2[CH:14]2[CH2:15][CH2:16][CH2:17][CH2:18][O:13]2)=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 513419766-(Bromomethyl)-1H-indazole hydrobromide

Product 1

HCID 186161856-(Bromomethyl)-1-(tetrahydro-2H-pyran-2-YL)-1H-indazoleYield 72%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A yellow suspension of 6-(bromomethyl)-1H-indazole hydrogen bromide (9.0 g, 43 mmol) (4-5) and 3,4-dihydro-2H-pyran (7.2 g, 86 mmol) in THF (200 mL) was heated at its reflux temperature for 2 hours. After cooling down to room temperature, the reaction mixture was stirred at room temperature for 12 hours under nitrogen. The reaction solution was diluted with methylene chloride (500 mL), washed with saturated NaHCO3, water and brine. After drying (MgSO4), the solvent was removed under vacuum to give a yellow oil. Flash chromatography yielded the title compound (6.6 g, 72%). TLC Rf 0.52 (80:20 of hexane-ethyl acetate); MS (electrospray) 295, 297 (M+1); 1H N MR (CDCl3) δ 1.57-1.84 (m, 3H), 2.16 (m, 2H), 2.55 (m, 1H), 3.75 (m, 1H), 4.01 (m, 1H), 4.65 (s, 2H), 5.71 (d, 1H, J=9.2 Hz), 7.44 (d, 1H, J=8.8 Hz), 7.59 (d, 1H, J=8.8 Hz), 7.73 (s, 1H), 8.00 (s, 1H).

Workup

  1. temperaturewas heated at its
  2. temperaturereflux temperature for 2 hours
  3. washwashed with saturated NaHCO3, water and brine
  4. dry with materialAfter drying (MgSO4)
  5. customthe solvent was removed under vacuum
  6. customto give a yellow oil

Sources & evidence

ORD record
ord-b482397100634f42b9ce19f445a4a6bb
Source dataset
uspto-grants-2003_01
Patent number
US06506760B1

Reaction notes

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